The proposed research program described below represents a continuation of efforts initiated several years ago in the area of synthetic organic chemistry. The investigations are designed to develop novel and useful synthetic methodology for the construction of naturally occurring materials having complex, nitrogen containing, polycyclic skeletons. The specific problems under study include the use of amino-Claisen rearrangement reactions of N-Vinylisoquinuclidenes for synthesis of representative members of the Indole alkaloid family and the development of novel methods for preparation of 2-azadienes and their transformation via intramolecular Diels-Alder reactions to chemotherapeutically interesting substances possessing the hydroisoquinoline ring systems. The focus of our continuing work in these areas is the development of new and useful chemistry which is broadly applicable to the synthesis of naturally occurring and/or medicinally interesting products.